


Sittin' in a Tree

by Pinkerton



Category: Check Please! (Webcomic)
Genre: 5+1 Things, M/M, Multi, Recreational Drinking, bros kissing, lots of bros kissing
Language: English
Status: Completed
Published: 2015-12-01
Updated: 2015-12-01
Packaged: 2018-05-04 07:26:38
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,638
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5325668
Author URL: https://archiveofourown.org/users/Pinkerton/pseuds/Pinkerton
Summary: <blockquote class="userstuff">
              <p>Bros helping bros. Five kissing lessons plus one perfect kiss.</p>
            </blockquote>





	Sittin' in a Tree

**Author's Note:**

> If you are Kent averse, you can skip the third lesson, but his role is pretty much just a remix of Epikegster. 
> 
> Pairings for each section at the end. 
> 
> Ngozi created these guys, I am just arranging them so that they happen to make out with each other.

Lesson One: Advanced Technique

Later, if asked, Ransom and Holster will explain that the logistics leading up to their first threesome were complex and required masterful wheeling and the most nuanced of flirting to seal the deal.

What really happens is that during a party sophomore year, Ransom starts flirting with a fellow bio major named Kelsey in the kitchen, which leads to Holster wing-manning for him in the living room, which then leads to the three of them sitting on the couch, Ransom kissing Kelsey’s neck while Holster whispers in her ear. Kelsey says “Fuck, you’re both hot,” puts down her beer, grabs each boy by a wrist and takes them upstairs to the attic. 

(She had originally tried to take them to the nearest bed she could find, which was Jack’s, and Ransom and Holster still try to use the fact that they redirected her as a bargaining chip in arguments.)

She breezes through the door at the top of the stairs and throws her shirt to the side before dropping into the lower bunk with a bounce and giggle. Ransom and Holster both stop at the threshold, eyes wide. Sure, they’d drunkenly talked about this, but now that it was happening...

...they look at each other, grin, and high five, scrambling toward the bed while stripping. 

Things progress nicely, with Kelsey on her back between them, turning to kiss and touch one boy, then the next. A few minutes later, though, and she is definitely favoring Holster. Ransom inches closer, running his hands through her hair, gently cupping her face and trying to tip her toward him. 

“Mmmm,” she says, pressing even closer to Holster. 

“Awwww,” Ransom says softly, which is enough to get Holster’s attention.

“Bro?” he says breathily, pulling back from Kelsey and lifting his head to look at Ransom. “Why sad voice? There’s no sad voice in threesomes.”

“You’re getting all the love, man,” Ransom says.

Kelsey wriggles between them, turning to look at Ransom. “Justin, you’re so hot, but Adam is like, the best kisser.”

“Oh?” Holster says, a grin spreading.

“I don’t—“ Ransom starts before Kelsey interrupts him.

“Justin, no, you’re good too, but since I’m comparing in real time, I gotta say, Adam’s better.“

“Wait, wait, wait,” Ransom says, sitting up. “For real?”

Kesley flops back onto the bed. “Yeah, it’s amazing.”

“Holtzy,” Ransom says urgently, leaning over Kesley, “kiss me.”

Holster’s brow furrows a little, but he sits up to meet Ransom and gives him a quick peck.

Ransom makes a frustrated noise. “No, like you mean it, dickbag.”

Holster huffs before he reaches out and hauls Ransom in, kissing him deeply, one big hand cradling the back of Ransom’s head, the other stroking his cheek, angling his head a little more to the left. Ransom groans when Holster uses his teeth to nip at his bottom lip. Kelsey gasps. When they finally pull apart, they’re both panting. 

“Bro,” Ransom says, staring at Holster like he’s never seen him before. “What? How?”

Holster shrugs. “Sophomore year of high school. Emily Bowers.”

“The senior cheerleader?”

“You mean the girlfriend you think I made up?”

Ransom shakes his head. “I am so sorry to have ever doubted you. But you gotta teach me how you do that.”

“Yeah,” Kelsey pipes up. Ransom and Holster glance up to where she’s resting against the headboard, hand down her jeans. “Teach him good, Adam.”

“Yeah, _Adam_ ,” Ransom smirks, batting his eyes at Holster. “Teach me goooo—“

Holster kisses the smirk clean off Ransom’s face.

Kelsey’s long gone when they wake up the next morning, but she did use her lipstick to write “A+ most improved” on Ransom’s chest. 

 

Lesson Two: Long Term Planning 

The keg ran dry hours ago, Jack went to bed, Holster went off with a girl from the swim team, and no one can find Johnson. That leaves Shitty and Ransom passing a joint back and forth on the roof, Shitty listing into Ransom’s side, talking with his hands. During a pause, he slumps heavily against Ransom, turns toward him, and starts kissing his neck. 

“Bro,” Ransom says. “You do this every time you get schwasted.”

“Do not,” Shitty says, moving up to Ransom’s jaw.

“You are the fucking cuddliest, sluttiest drunk in the world man. Is there a single person on the team you haven’t attempted to make out with while drunk?”

“Do the coaches count?” Shitty asks.

“Ugh, mental picture, gross,” Ransom says. 

“Aww, c’mon Rans,” Shitty says, kissing right below Ransom’s ear. “I’m the perfect amount of drunk and stoned for some low key making out, and you’re the only one here.”

“Be still my heart,” Ransom says, but then again…Holster is out for the night and the girl Ransom had spent the night hitting on had cleared out early to take her too drunk roommate home. Ransom insisted on walking them both back to the dorms and got her number in return, but that’s a long shot at a future date. 

Shitty is here, and warm, and doing kind of interesting things to Ransom’s earlobe.

“Eh, whatever,” Ransom says, turning his head to meet Shitty’s mouth with his own.

The kiss is off center. Ransom “hmms” and moves his head down, but Shitty goes sideways. Ransom chases his mouth, but Shitty over corrects. They finally get their lips more or less lined up, but then Shitty’s tongue is just everywhere. 

“Ugh,” Ransom says, pulling back. “You suck at this.”

“What?” Shitty says, blinking slowly.

“Let’s try it again,” Ransom says, leaning in cautiously, tilting to the left a bit.

Shitty mirrors him, but too fast, and their noses smash together. 

“WHAT THE ACTUAL FUCK?” Ransom yells, jerking away.

“Keep it down, assholes, we have practice in…tabernac, it’s Saturday, just shut the hell up,” comes from Jack’s window.

Ransom rubs his nose. “Shits, we gotta sober up and work on this.”

* * *

Two plates of pancakes and a massive carafe of diner coffee later, and Ransom hits upon the magic combination of words to convince Shitty to step up his make out game.

“Should you ever manage to land her, Lardo will never put up with that shit.”

Shitty’s eyes go wide. 

* * *

Turns out that with proper motivation, Shitty is a fast learner. Saturday Mario Kart and Make Out Clinic only runs twice before Ransom declares him suitable to set loose upon the masses. They never discuss it, or kiss, again. 

Ransom still thinks about that moustache every now and then, though. 

 

Lesson Three: Loose Lips and that Sinking Feeling

Kent sees it all going south the minute he mentions Vegas. Kent hears “I don’t know, okay” coming out of Jack’s mouth and then he’s pressing his own to it, desperate to delay everything crashing down around him, the final death knell to the stupid fantasy he’s been nursing for years—Jack and him together again, Jack and him demolishing one NHL record after another, Parse and Zimms, Zimms and Parse…

Jack tastes like cheap beer, which is expected, and cinnamon, which is not. He kisses the same, all teeth and tongue and spit, and for a second, Kent could swear they’re 17 again. He pulls back, wipes his finger under Jack’s chin, and laughs, whispering against Jack’s ear. “You kiss the same, Zimms. College not teaching you anything?”

“ _Pars--_ ,” Jack moans, loud, kissing Kent again while his name is still on his lips. 

“Here,” Kent says under his breath, against Jack’s mouth, “move your—no, not like…Jesus, Zimms, slow down…fuck, you haven’t changed at all, have you—“

The words are barely out of Kent’s mouth before Jack goes rigid in his arms, and no, Kent was wrong before. That was the death knell. Jack’s changed so much Kent doesn’t even know him, but he had to open his stupid mouth--

“Kenny, I can’t do this.”

And then it all goes to hell.

* * *

It’s mid-January when Jack makes it back to the Haus after holiday break, and it takes an entire 43 minutes before Shitty walks into his room, shuts the door, and sits on his bed, arms crossed.

“Shits—“ Jack tries.

“My beautiful baby boy, don’t even start with me.”

Jack sits down at his desk, shoulders slumped. “I fucked up.”

“Parson?”

“Yeah.”

“Doubtful. What happened?”

Jack lets his head drop down toward his chest and runs his fingers through his hair. “It’s just…what if I haven’t really changed?”

“Bruh—“ Shitty starts as Jack blurts out “What if it’s all been for nothing? What if I’m the same as I was before…Shitty, I can’t…” and Shitty might be tough, but Jack doubting the insane courage he walks with every single day is about to break him.

Shitty shakes his head, and moves to thump his chest. “Jack Laurent Fucking Zimmermann, you bring it in.”

Jack does, leaning into Shitty hard enough to knock them both fully onto the bed. Shitty wraps one arm around Jack’s shoulders, squeezing hard, and strokes his hair with the other. “C’mon, man. Of course you’ve changed. Look at this gorgeous display of trust and love, my brother. The Jack I met as a frog would have buried this deep until he lost his cool on the ice and ended up in a five-minute penalty. You’ve changed. You know it.”

“Shitty,” Jack mumbles against his chest. “What if I’m a bad kisser?”

Shitty, for the first time Jack can ever remember, is silent. Jack stiffens in his arms. 

“That’s a hell of a non sequitur,” Shitty says.

Jack groans, and buries his face in Shitty’s shoulder. His words come out muffled. “It’s just…if I think I’m good, but maybe I’m not, how would I know if I think it’s ok? Like, I know I’m good at hockey. I know it. But other stuff…forget I said anything.”

“Hey, hey, hey,” Shitty says. “Sit up for a sec.”

“Huh?” Jack says as he pushes away from Shitty, rubbing the back of his hand over his eyes.

“I’m gonna lay one on you, okay?”

“Wha—“ Jack says, before he’s cut off by Shitty’s mouth on his. Jack freezes for a long second, but just as Shitty is about to give up, he starts kissing back.

Unlike the multiple fan fics Ransom and Holster gleefully read aloud to Shitty their freshman year, Jack Zimmermann does not kiss like he plays hockey. There’s fire, sure, but no finesse, and, ow, too much biting. 

It’s cool, though. Shitty has a game plan.

He takes Jack out for pancakes and coffee, and lays out how their Saturday afternoons of Mario Kart and Make Out Clinic is going to go.

By the fourth Saturday, Jack has Shitty pressed against the couch, panting. “Okay, okay,” Shitty gasps. “You’re cured.”

Jack grins and, Shitty’s hand to god, the motherfucker winks at him.

 

Lesson Four: Conceptual Face Sucking

After a random party, somewhere on Samwell campus, a sophomore communications major is trying her hardest to pretend to be asleep while overhearing the following exchange from the bunk below hers:

"God Johnson, you kiss like, like-"

"Like the benefits of remaining an ill-defined character?"

“What?”

“Like a narrative device to fill in a slot in a preconceived yet ultimately arbitrarily chosen list of events?”

“…can I just touch your abs some more?”

“Sure thing, babe.”

The roommate sighs, putting her pillow over her ears. She is so getting a single next year.

 

Lesson Five: California Beaming

Bitty’s had just enough beer to feel warm and loose. Chowder’s had two—he’s flushed and has been talking about Farmer for ten straight minutes.

“—plus she smells really, really good, like, when my pillow smells like her hair it is the best thing ever! Um, sorry, maybe that’s an over share?”

Bitty smiles. “It’s sweet, Chowder. I’m happy for you two.”

“She’s the best person I’ve ever dated. Hey, when are we double dating with you and Charles?”

Bitty sighs. “Well, I’m sure y’all can come to a rugby game, but it would only be a date for you two. We’re gonna just be friends.”

“Awww,” Chowder says, frowning. “What happened?”

Bitty shrugs. “He’s super nice, but there wasn’t really a spark.”

“I hate that,” Chowder says. “Like, when you think it’s gonna be great, but then you kiss and it’s just so flat, and you know it won’t work. You just know.”

“Well,” Bitty says, fiddling with the tab on his beer can. “We didn’t get even that far.” 

Chowder leans down and assesses Bitty’s face. “You’re sad about it?”

Bitty shifts in his seat. “Not about Charles so much but—um. I just expected that after almost two years at Samwell I would have at least…you know.”

Chowder raises an eyebrow.

“Kissed-a-boy,” Bitty gets out in a rush.

“You haven’t kissed a boy yet?” Chowder asks. 

“No.”

“Have you kissed anyone?”

Bitty rolls his eyes. “Yes, Chowder, I went on dates in high school. Kissing those girls was fun, but…they never made my toes tingle, you know?”

Chowder considers this. “You could kiss me!”

Bitty grimaces. “Chowder, no.”

“Farmer’d be cool with it.”

Bitty takes a moment to process that. “Chowder, dear goalie child, you are the sweetest boy. But I’m gonna take a pass, honey.”

Chowder shrugs. “Okay. Want another beer?”

“Lord, yes,” Bitty says.

* * *

Three days later, there is a chill gathering for the volleyball team at an apartment off campus, which the hockey team more or less turns into a rowdy disaster within 10 minutes of their arrival. Bitty’s deep in a conversation with Dex when Chowder comes out of nowhere, tugging a boy behind him. “Bitty, this is Sami, he lives here and he likes the pie you brought!” Chowder gets out in one breath while he pulls Dex to his feet and away with him. “You guys should talk I’ll see you later bye!” 

Sami laughs and leans toward Bitty, talking loud over the music. “Chowder says it’s a chess pie but what on earth does that mean?” 

Bitty laughs, “Honey, what I can tell you about chess pie would fill a book. Have a seat.”

Sami has curly black hair and his eyes crinkle when he laughs. Bitty is the first southerner he’s ever met, and they end up tucked away in his room, talking for hours. When Sami kisses him, Bitty’s toes don’t exactly tingle, but they do curl, just a little. 

+1 Final Exam

It takes four years, a Stanley Cup, and several late night talks on the phone, but Jack and Bitty finally get it together and go on a date. Jack planned every cliché possible—a stretch limo, champagne, dinner at the ritziest steak house in town, and drinks after in a jazz club. Bitty rolled his eyes at the beginning, but by the second course of dinner he can’t stop grinning. The night is perfect, from the way Jack pulls out his chair, to the way he puts his arm around Bitty at the club, and finally, when he drops Bitty off at his hotel, stopping in front of the door. “I had a lovely night, Eric,” Jack says in monotone, keeping a straight face for all of two seconds before laughing. 

Bitty snorts, he can’t help it. “Are you gonna kiss me or what, Zimmermann?”

“Pushy, aren’t you?”

“It’s been four years, Ja—“ and Jack leans down and kisses Bitty, and it’s soft and sweet and perfect, until it turns hot, and Bitty isn’t sure how he ends up pushed against the door, and when Jack finally pulls back they’re both breathing hard, eyes glassy. 

“Shit,” Jack says.

“Oh my,” Bitty says.

“Bittle,” Jack says, dipping down to kiss him again.

Bitty knows, right then, from the top of his head to his tingling toes, that he will never kiss another boy ever again.

**Author's Note:**

> Pairings:
> 
> Lesson One: Ransom/Holster/Female Undergrad  
> Lesson Two: Shitty/Ransom  
> Lesson Three: Jack/Parse, Jack/Shitty  
> Lesson Four: Johnson/Female Undergrad  
> Lesson Five: Bitty/Male Undergrad  
> +1: Jack/Bitty
> 
> Much love to muchandquick, who came up with the Johnson part and also sent me the following message when she woke up to all my IMs about this story:
> 
> Me: (goes on and on about hockey boys kissing) I'M WRITING THIS  
> Her: It is 8:30 on a Saturday, you pistachio
> 
> I'm agrossunderstatement on tumblr.


End file.
